Third Times The Charm
by eriridan
Summary: It takes Dean three times to realize he just might like his brother in an entirely different way than he should, only to realize that Sam feels the same, too.


**A/N:** yes hello this is my second fanfic for wincest/spn  
i hope you enjoy it uwu  
ever since i wrote fluffy things for sam and dean i figure i ought to write sex sooner or later so here it is  
thank you for reading and dealing with my rambling!  
ps also there might be some errors but right now i have a fever of 103.6 so please do bare with me!

Dean doesn't know how to describe the twist in his gut when he touches his brother's face, when their hands brush as they walk down the street, or even that indescribable heat he's sure he's felt before when Sam walks out of the motel bathroom in nothing but a towel. He doesn't know what to call the feeling he gets when they hug, the sensation of Sam's body against his, or even the tightness he gets in his chest when his hands run across his baby brother's broad shoulders, the way they seem to fit there so perfectly.

He doesn't know what to call the feeling he gets when Sam smiles at him, when he throws his head back to laugh or sing; doesn't know what to call the feeling that builds in his gut when he feels his brother's body heat mingle with his own in the Impala or even on those rare occasions they share a bed. Dean especially doesn't know what to call the feeling that spreads throughout his chest when Sam says his name. He doesn't know what to call the feeling for any of that, doesn't even know how to describe it to himself. Though, he's sure there's a word for it.

The first time it occurs to Dean that maybe, just _maybe_ he likes his brother in an entirely different way than he should, he only freaks out for five minutes; which, in all reality should freak him out even more. He'd just passed by an old Chevy cavalier only to see a guy and his girl making out in the front seat, his grabby hands roaming all over and her own equally grabby hands tugging on his hair as if she couldn't get enough. The sight of it made him chuckle, a smirk taking over his lips as he thought '_that could be Sammy and me_.'

After that thought, it didn't take long for him to imagine it—him leaning over to Sam, a hand settling on his brother's neck to grab his attention, fingers soft against the sudden pulse as his lips began to get too eager to be against Sam's. It didn't take him long to imagine the way Sammy's breath would hitch slightly, the way his eyes would widen unexpectedly; didn't take long until he could almost feel his hands about his brother's body, large hands in his hair and a noise of frustration from underneath him because Dean's hair simply isn't long enough to tug on.

When Dean realized the soft hum of a moan he was hearing was his own, however, he snapped out of it, brows tugged upward in surprised as he cleared his throat loudly. He blinks a few times before pulling off to the side of the road, rubbing his hand against his chin as he focused on anything but his thoughts, _anything_ but the heat coming from his half hard member and the pulse of his blood hammering in his eardrums.

Though, what surprised him most was how quickly he got over the little freak out. Yeah, most guys don't imagine making out with their younger sibling in the front seat of his car, or how it would feel to have your hands on them and vice versa; but Dean couldn't find it in him to feel sorry or guilty, or even regret it. It seemed strange to him, though, that he couldn't begin to feel the emotions of shame that he probably should have. A small _huh_ come from him as he pursed his lips with a tiny shrug, starting the Impala and easing back onto the road to get back to the motel where Sam was waiting.

The second time it occurs to Dean that he just might like his brother in an entirely different way than he should, he's waking up from a dream. The heat radiating his body is almost too much for him, the pulse of his hard-on seeming to rage in his ears. A quiet groan escapes him as he glances over to the other bed where Sam's still fast asleep (mouth open and drooling, hair messy with tossing and turning); and suddenly it's like he's back _in_ the dream.

Dean can almost feel his hands gliding smoothly against Sam's chest, can almost _feel _the sensation of his brother's thighs twitching against his hips as he settles himself on his knees between them. It's almost like he's right up against him, feeling Sam shudder and twitch and give out a shaky laugh under him as he murmurs words of _yeah, Dean, _and _oh God, finally, finally, come on;_ and he gives a small laugh, fingers moving inside his baby brother as if to keep him at bay.

Sam's got one of his classic bitch faces on, his face flushed and skin covered in little bite marks and forming hickeys. Dean's not fully satisfied though—Sammy shouldn't be making such a face during this of all things; so he takes it of himself to drive his fingers deeper, bending them upward to rub against that certain place that makes Sam groan out in response, his entire expression changing completely.

A small _"Jesus Christ,"_ slips through Dean's mouth as he pulls himself out of his thoughts and out of bed. The image of Sammy's face filled with pleasure and heat and outright desire for _him _was almost too much for his aching member as well as himself. Heaving out a low moan, Dean navigates himself across the room carefully, keeping watch out of the corner of his eye for any movement from Sam before he shuts the door to the bathroom; hand already halfway down his pants.

The third and final time it occurs to Dean that he definitely likes his brother in an entirely different way than he should, Sam's lips are on his. They're parked on the side of the road per Sam's request, something about having to pee and not willing to risk a bladder infection if he held it in too long. Dean had rolled his eyes at that, however he did as Sam requested, easing the car off to the side of the road and to a stop, putting her in Park.

"Aren't you gonna go take a piss, Sam?" Dean asked, his brows pulling together in irritation. Two minutes had passed in silence and Sam was still seated beside him, eyes locked on the glove department. "Come on, man," he continued. "If you don't have to pee anymore let's just get going and—"

"Look at me, Dean," Sam says, the tone of that voice making Dean's skin crawl enough that he's almost expecting something—_anything,_ possibly his own desires and wants and _needs_; he swallows on impulse, shifting himself to face his brother while trying to act like it's the last thing he wants to do. And even though, in the back of his mind, he was expecting it, the fact that it happened is something that'll never leave him.

Dean watched as Sam leaned to him, watched as his brother closed his eyes half way and watched the shiver that ran through Sam as his lips were pressed against his own. He responded almost immediately, giving in and groaning with need while taking Sam's face in his hands, pulling him closer and leaning in himself to force his brother's mouth open. When Sam realized what Dean was trying to do, he went with it, opening his mouth the tiniest bit—and Sam moaned (flat out _moaned_) at the feel of Dean's tongue in his mouth, against his own tongue.

"_Christ,_ Sammy," was breathed as Dean broke the kiss, lips mouthing along the line of his brother's jaw, down his neck and a bit to the left to plant kisses and small sucks on his collarbone. "Dean, _Dean,_" was murmured back in return, little breathy laughs coming from Sam's mouth as he pulled his brother closer, directing his attention back on Dean's lips before he guided a hand downward, chuckling into the kiss before pulling back, leaning his forehead on Dean's shoulder. "You're hard."

He snorted as he lead his own hand to Sam's crotch, turning his head the tiniest bit to bite at his brother's ear. "You too, Sammy; you're hard too," Dean told him, the smirk on his lips playful as he presses the palm of his hand against the hard bulge of his brother's pants. It caused a low moan to sound from Sam, his hips pushing as best as they could against Dean's touch in this position.

"Dean—" Sam started, breath heavy and warm against his brother's cheek. Dean felt Sam's fingers play with the button of his pants, felt the twitch of his member at the thought of those fingers around it. "We—We have to," he paused here, leaning away from Dean to reposition himself. "—move, come on, Dean," Sam urged, pressing himself against the passenger door so Dean could lift his legs hurriedly while Sam stretched his own out.

A few more moments and curses later, Sam's legs were on either side of Dean's hips and Dean's own legs were under Sam's, their crotches practically rubbing against each other. Their breathing mingled as they fumbled at each other's pants, fingers focusing on getting the buttons undone. Dean let out a pleased sigh as Sam's fingers curled around his aching length; and Sam did the same, his breath shaky and voice sounding so relieved as he breathed, "_finally, finally, oh God, Dean, I'm—"_

"Yeah," Dean murmurs, brows furrowed together as he leans his forehead against Sam's, shivering at the feel of the head of his penis against his brother's. Dean's so wrapped up in what they're doing that he forgets where they're at, but he couldn't care less—this is what he's been waiting for. He rubs their penises together gently, fingers wrapping around his and Sam's length as if to draw them closer. He's pressing kisses to Sam's mouth that Sam returns just as eagerly, his thumb running along their heads to spread the pre-cum that gathered there. "Me too, Sammy, me too—"

Months have passed since then, and still Dean holds close to no regret, shame or guilt; especially not when they're kissing each other, touching each other or calling each other's name when they hit their climax. They haven't had sex, no—just handling each other in the late hours after a hunt, occasional blowjobs and fingers in places they probably shouldn't be. It only occurs to Dean about how much he _wants_ Sam when they're spooning, and he's got a hard on and he's unsure if Sam's awake or not but nonetheless Sam's moving back against it, mumbling things that make Dean's situation worse.

That's happened more times than Dean would like to admit, and each time it happens it's always the same. He has to slip out of bed carefully as though to try not to disturb Sam in his sleep—after all, Dean's not aware if Sam realizes what happens while they sleep together, his front pressed against Sam's back. So he tries to be as quiet as possible as he gets out of bed and walks across the room to the bathroom; tries to be as discreet as possible when he's leaned against the door, fingers curled around his member as his hips twitch forward; and it's all he can do not to groan in need, his imagination of how it would feel to be _inside_ of Sam almost too much for him to handle.

Dean's so used to that being the routine that he's unsure what to do when one night, Sam asks, "Do you want... to?" in a whisper, his hips moving the tiniest bit against his hard-on. Dean couldn't help but think, "_this little bitch, he knew all along?"_ yet he doesn't say it aloud, only lets out a breath against Sam's neck and mouths kisses along his naked shoulder, giving out a nod as a familiar warmth spreads through him when his brother chuckles, turning over on his back as Dean shifts to settle between his legs.

They kiss for what seems like forever, tongues rubbing against each other's softly as their fingers and hands are gentle against each other's bodies, coaxing off the small amount of clothing they have on; and even though they both know the other is nervous, Sam comforts Dean with kisses and reassuring touches—and Dean returns the gestures, whispering _I love you'_s and _oh, god, Sammy, I've been waiting for this, I have, I have._

Sam's breathing out laughs and he's returning those words in earnest, giving Dean's shoulders and his neck little bites and sucks, taking Dean's wrist in his hand to guide it down between them. Dean can feel the way his brother's length is twitching, the way the pre-cum is gathered at the tip; he can hear the way Sam's breath eases when Dean's hand is on it. "Ready, Dean, come on," he urges, bumping his forehead against his brother's as he takes Dean's hand away from his member, going down further.

Dean lets out a sigh, middle finger already against Sam's entrance—and he pauses, planting a kiss against Sam's collarbone before turning away. He can't help but laugh at the way Sam hisses, his classic bitch face on board. "Just gotta get the lube, Sammy," he tells him before digging through his duffle. Dean settles himself between Sam's legs once he's got the lube, spreading the slippery substance on his fingers before tossing the bottle within reach beside him.

He slides his finger inside his brother carefully, watching Sam's face for any sign of pain he might give off; when the sign doesn't come, Dean takes it of himself to extract his finger carefully only to push it back in, giving out a shaky sigh at the way Sam tightens around him. His brother's face as it is was something he's never seen before—lit with pleasure and desire and need for _him, _only for _him_ and Dean can't help the twitch that comes from his already half hard member, the way his chest tightens as if his heart's about to give out.

"Christ, Sammy," he breathes. Dean's moving his finger faster, his other hand rubbing Sam's shaking thigh in comfort as he adds another finger, bending them slightly and pushing forward to explore the inside of his brother. Five more minutes of that and Sam's moving his hips impatiently, brows drawn together as he looks at Dean through half closed eyes. "Dean, Dean—" he urges, heaving a sigh at the sudden hand on his aching length. "I'm ready, Dean, ready—"

Dean shushes him, bending to plant kisses at his neck, his collarbone, shoulders—he travels downward, kissing at Sam's chest and his abs. He takes his fingers out of his brother when his lips reach fine hairs just above Sam's twitching penis, and he kisses there, too, lapping pre-cum in a way that makes Sam lift his hips up into it. Dean laughs, his breath surely hot against his baby brother's skin. "I'm gettin' there, Sammy," he reassured him, standing straight once more to adjust himself and his brother, taking a moment to cover his member with more lube before directing his attention back to Sam.

A moan escapes them both as Dean presses the head of his penis against Sam's ass, and he pushes back against it, moving his hips as though to encourage Dean to enter already. That causes a shaky laugh to come from Dean, his brow twitching as he slides a hand between them, adjusting his member as Sam rests his calves on Dean's shoulders; Sam's own hands venture downward to spread himself open for his brother, a groan passing his lips when he feels Dean against his entrance, the tip slick with pre-cum and lube and _goddamn it_ Sam just wants to beg, he's been waiting for this for years and—

"Tell me if it… hurts, Sammy?" Dean says then, though it's more of a question than a statement. Sam nods harshly, his breath hitching as he feels the tip of his brother's penis press against him. A groan escapes him and he tries his best to relax, the sensation of Dean _in_ him almost too much to bear. Sam moves against his brother as if to tell him that he's alright, that the feeling is good and great and he's high off it, high off _him_ and then Dean pushes in some more and it's all Sam can do to _not_ touch himself, to not moan Dean's name and tell him to hurry up.

By the time Dean's all the way in, they're both groaning and sweating and shaking against each other; and it's a moment before Dean moves, murmuring questions of _"does it hurt, Sammy?" _and _"Christ, Sammy, do you feel this, do you feel this good, Sammy, do you?"_ and Sam shakes and nods his head furiously, allowing his back to arch and his hips to grind against Dean.

He's being careful with Sam, pulling out carefully and thrusting back inside him quickly, grinding his hips against the back of his thighs in a way of comfort, it seems. Sam's giving out small moans that are accompanied by Dean's own, the light sound of skin-on-skin slapping from thrusts filling the air along with their moans. "Dean, Dean—" Sam's breathing out, a shaky sigh leaving him when Dean thrusts deep, the tip of his member brushing against that certain place in him. "Sam, _Sammy,_" Dean's saying, sliding a hand in front of him to focus on his brother's twitching member.

Dean's thrusting against him, hand working gently at Sam's penis; fingers smooth as they gather pre-cum to cover the shaft with, thumb careful as it brushes against the slit and _Jesus Christ _he's never been this gentle, this careful, this _loving_ toward anyone before. It's all Dean can do to _not_ let himself orgasm right then and there when his brother tightens around him, cum covering his fingers and slipping between his palm and Sam's penis; he strokes him through it, a groan escaping him as he moves his hips a bit faster, just a bit more harder as he watches Sam's face—he's going through orgasm and it's all because of _Dean,_ all because of him and _goddamn it_ he feels himself slipping and—

"_Sam,"_ was moaned as he came, and Dean leans down, hips still moving against Sam to ride out his orgasm as he kisses him, groaning lightly and biting at his lips before backing away. Moments later Dean's hands are moving about Sam's body in a way of comfort as he slips out of him, which causes a protesting groan to sound from his lips; that causes Dean to laugh as he settles beside him on the bed. Sam gives a small smile as Dean scoots closer, only to raise an eyebrow as his brother makes a face. "You reek, man."

He rolls his eyes, turning his back to Dean as he settles comfortably on his side. "You do, too, jerk," Sam tells him in irritation; and Dean lets out a laugh, scooting closer than before as he bends his knees to settle along the back of his brother's legs. "Bitch."


End file.
